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Chlorine-substituted polythiophene derivatives and solar cells

A technology of polythiophene derivatives and solar cells, applied in circuits, photovoltaic power generation, electrical components, etc., can solve the problems of low open circuit voltage, limited energy conversion efficiency, etc., and achieve the effect of high open circuit voltage

Active Publication Date: 2021-09-03
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the strong electron-rich properties of the thiophene unit, P3HT has a higher highest occupied molecular orbital (HOMO) energy level (ˉ-4.90eV), resulting in a lower open-circuit voltage for P3HT-based solar cells, which limits its energy efficiency. Further improvement in conversion efficiency

Method used

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  • Chlorine-substituted polythiophene derivatives and solar cells
  • Chlorine-substituted polythiophene derivatives and solar cells
  • Chlorine-substituted polythiophene derivatives and solar cells

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preparation example Construction

[0025] Preparation of raw materials M1 and M1',:

[0026]

[0027] (M1) and (M1'); wherein R is a branched alkyl chain in the formula (M1), and R is an alkyl chain in the formula (M1').

[0028] Preparation of raw materials N1(II-1)(II-4), N2(II-2)(II-5), N3(II-3)(II-6):

[0029]

[0030] Preparation of product:

[0031]

[0032]

[0033]

Embodiment 1

[0034] Embodiment 1: (2-butyloctyl)-2-bromothiophene-3-carboxylate

[0035]

[0036] 2-Bromo-3-carboxythiophene (1.50g, 7.28mmol), DCC (0.87g, 8.74mmol), DMAP (0.23g, 2.55mmol), 2-butyl-1-octanol (2.70g, 14.50mmol ) was dissolved in 50 mL of dichloromethane and stirred at room temperature for 24 hours. Then it was poured into water, filtered, and the filter cake was washed several times with dichloromethane. The filtrate was collected, washed three times with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was spin-dried, and the crude product was subjected to silica gel column chromatography (the eluent was petroleum ether (PE): CH 2 Cl 2 =6:1) Purified to obtain colorless liquid (2-butyloctyl)-2-bromothiophene-3-carboxylate. The structural characterization data are as follows: 1 H NMR (CDCl 3 ,400MHz): δ(ppm)=7.92(d,J=1.6Hz,1H),7.52(d,J=1.6Hz,1H),4.14(d,J=5.6Hz,2H),1.75-1.66(m ,1H),1.45-1.19(m,16H),0.85-0.90(m,6H).

Embodiment 2

[0037] Example 2: (2-hexyldecyl)-2-bromothiophene-3-carboxylate

[0038]

[0039] 2-Bromo-3-carboxythiophene (1.50g, 7.28mmol), DCC (0.87g, 8.74mmol), DMAP (0.23g, 2.55mmol), 2-hexyl-1-decanol (3.50g, 14.50mmol) Dissolve in 50 mL of dichloromethane and stir at room temperature for 24 hours. Then it was poured into water, filtered, and the filter cake was washed several times with dichloromethane. The filtrate was collected, washed three times with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was spin-dried, and the crude product was subjected to silica gel column chromatography (the eluent was petroleum ether (PE): CH 2 Cl 2 =6:1) Purified to obtain colorless liquid (2-hexyldecyl)-2-bromothiophene-3-carboxylate. The structural characterization data are as follows: 1 H NMR (CDCl 3 ,400MHz): δ(ppm)=7.94(d,J=1.6Hz,1H),7.54(d,J=1.6Hz,1H),4.17(d,J=5.6Hz,2H),1.78-1.68(m ,1H),1.46-1.19(m,24H),0.85-0.90(m,6H).

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Abstract

The invention belongs to the technical field of organic photoelectricity, and in particular relates to a chlorine-substituted polythiophene derivative and a solar cell. Chlorine-substituted polythiophene derivatives are characterized in that, as shown in formula (I): wherein, X, X' are H, F or Cl; R is C8-C24, and n is a repeating unit. This application introduces electron-withdrawing groups into thiophene compounds, which can lower the HOMO energy level of polymers. Chlorine atoms have strong electronegativity, and the introduction of chlorine atoms into conjugated polymers can achieve lower HOMO energy levels. More importantly, chlorine-substituted polymers are easy to synthesize and can be obtained from commercial raw materials through relatively simple synthesis methods.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectricity, and in particular relates to a chlorine-substituted polythiophene derivative and a solar cell. Background technique [0002] Organic solar cells have the advantages of low cost, light weight, flexible devices and large-area devices, so they have attracted extensive attention (Science 1995, 270, 1789-1791; Acc.Chem.Res. 2009, 42, 1709-1718; Chem . Rev. 2015, 115, 12666-12731; Nat. Photon. 2015, 9, 174-179; Nat. Photon. 2012, 6, 153-161; J. Am. Chem. Soc. 2015, 137, 14149-14157). In recent years, with the development of A-D-A small molecule acceptor materials based on fused ring units, the energy conversion efficiency of organic solar cells has increased rapidly. This type of small molecule receptor material has strong absorption in the visible light region, and through rational molecular design, the absorption spectrum of this type of receptor material can be extended to the near...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/42H01L51/46
CPCC08G61/126C08G2261/124C08G2261/1426C08G2261/146C08G2261/3223C08G2261/122C08G2261/414C08G2261/91C08G2261/18H10K85/113H10K85/151H10K30/00Y02E10/549
Inventor 李淼淼耿延候王琪
Owner TIANJIN UNIV
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